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Little is known about the early life of Diego Velázquez.[2] He was born in Cuéllar c. 1465, in the Segovia region of Spain. Velasquez was known for his hate of manual labor from a young age. This reason helped push Velazquez toward wanting to become a conquistador. Diego Velazquez was a part of the Spanish military, serving in Naples, and then returning to Spain to serve in Seville. Velazquez was met with all the excitement from Christopher Columbus's first voyage to the new world, so Diego made sure he was on the second voyage of Christopher Columbus.

Velazquez settled on the island of Espanola, where he befriended the Governor of the indies Bartolome Colon. Colon took a liking to Diego and when Colon had to leave the island for any period of time would make Diego acting governor of the Indies. Velazquez squashed an Indian revolt in 1503 by sending a captain to a part of the island while he went and captured the king of the revolting Indians which ended the revolt. The Governor of the Indies at this time was Nicolas de Ovando, and after the revolt decided that five new towns should be built. Velazquez helped form three of these towns, the names of the towns were Salvatierra de la Zabana, Yaquimo, and San Juan de la Maguana. According to historian Troy S. Floyd, "Velazquez himself, reportedly wealthy in island terms by 1511, held encomiendas at Verapaz, Salvatierra de la Sabana, and Santiago de Caballeros, where he was in partnership with an unidentified encomendero in mining enterprises."[3]

He married the daughter of Cristóbal de Cuellar, who died soon afterwards. He never remarried.[3]:139

He was named to lead the expedition of conquest of Cuba in 1511, with 300 men, a three-year undertaking noted for its brutality.[4] He acted under orders from Diego Columbus, recently restored as Viceroy of the Indies. He founded a number of new Spanish settlements and cities on the island, first Baracoa in 1511 and then most notably Santiago de Cuba in 1514 and Havana in 1515. Velázquez was appointed Governor of Cuba.[5]:16 The new settlers did not wish to be under the personal authority of Diego Columbus, so Velázquez convoked a general cabildo (a local government council) which was duly authorized to deal directly with Spain, and therefore removed Velázquez and the settlers from under the authority of Columbus, their nominal superior. It was a precedent that would come back to haunt him with the Mexican adventures.

Noting the weakness of the natives, Velázquez authorized the importation of black slaves in 1513. He authorized various expeditions to explore lands further west, including the 1517 Francisco Hernández de Córdoba expedition to Yucatán (see: Spanish Conquest of Yucatán), and Juan de Grijalva's 1518 expedition.[5]:16,27 He was made the first Adelantado of Cuba with jurisdiction over the former Governorship of the Indies.[5]:126 He initially backed Hernán Cortés's expedition to Mexico,[5]:44–47 but pulled back his support before the expedition was scheduled to launch. Cortés disobeyed Velázquez's orders to disband his expeditionary force and left for Mexico anyway.[5]:56

Velázquez lost his governorship of Cuba in 1521, for his misuse of indigenous labor, but he was restored to office in 1523. At the time of his unexpected death in 1524 at age 59, he was "the richest Spaniard in the Americas," despite financial losses on the expedition of Francisco Hernández de Córdoba and of Hernán Cortés. He completed the successful conquest of Cuba, founded towns that remain important, made Cuba economically prosperous, and turned it into the staging point for expeditions of conquest elsewhere. [6]